Homes with Pools for Sale in Windsor County, VT

413 homes

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NEW 9 HRS AGO

ABOUT THIS HOME
Home with a Pool for sale in Windsor County, VT:
Nestled at the end of a quiet dead-end road, this 14.2 acre private homestead offers exceptional privacy, timeless New England charm, and direct access to over 560 acres of town-owned land—the Hurricane Forest and Wildlife Refuge. This property is a rare blend of seclusion, natural beauty, and convenience—a one mile drive to the intersection of RT 89 and 91, just 20 minutes from Woodstock and within easy reach of all Upper Valley amenities. The Colonial-style home boasts wide pine floors throughout combining classic craftsmanship with the efficiency and comfort of a 21st-century build. The Rumford fireplace in the living room provides a perfect spot for cozy winter evenings, whi

$924,900

4 beds3 baths2,640 sq ft

307 Remick Rd, White River Junction, VT 05001

First-floor bedroom • Spacious kitchen • Woodstove

NEW 10 HRS AGO

ABOUT THIS HOME
Home with a Pool for sale in Windsor County, VT:
Welcome to 55 Trickle Brook Drive, a charming and well-designed home offering three bedrooms and two full bathrooms, being sold fully furnished, and ideally located just about 10 minutes from Okemo Mountain and close to the Proctor-Piper State Forest. This inviting property blends comfort, functionality, and year-round recreation, with nearby access to hiking, mountain biking, and snowmobiling trails. Enter through a spacious mudroom with ample room for storing your outdoor gear. The main level features an open kitchen, living, and dining area with vaulted ceilings, wood floors, and a propane fireplace that creates a cozy gathering space. The primary bedroom with an en-suite bath is also lo

$475,000

3 beds2 baths1,572 sq ft

55 Trickle Brook Dr, Cavendish, VT 05142

Large deck • Covered deck • Covered porch

ABOUT THIS HOME
Home with a Pool for sale in Windsor County, VT:
Looking for a great investment project? This is a stylish home with great bones. There's a spacious mudroom/breezeway that connects the oversized 3 car garage, with huge loft to the house. Very large eat-in kitchen abuts a pass thru dining room featuring a sliding glass door to the back yard and wood stove. The great room/living room is the full width of the house with elegant built-ins. The garage loft has a number of possibilities with access from inside the garage and an from exterior stairs, plenty of windows and over 700 sq ft of space. And the yard! There's a gazebo beside the brook on the lower level, a pond that could easily be brought back to life. Did I mention the fairy garden!!

$210,000

3 beds2.5 baths2,208 sq ft

3134 Fay Brook Rd, Sharon, VT 05065

Large eat in kitchen • Sliding glass door • Huge loft

OPEN JAN 10, 10AM TO 12PM

ABOUT THIS HOME
Home with a Pool for sale in Windsor County, VT:
Antique home with space for friends & family to join you for some special Vermont time. Currently set up as a single-family home with five bedrooms & bathrooms, the flow of this house allows for privacy and socializing with the upstairs family room & lower living room. There is an attached barn with potential for finishing too as well as an attached garage for toys or cars. The back entry leads to the laundry room & the bright kitchen with a breakfast nook & into a dining room with a large built-in & a table to seat many, & then into a cozy living area with comfy furniture.

$369,000

5 beds5 baths2,375 sq ft

2335 Main St, Cavendish, VT 05142

Bright kitchen • Antique home • Attached barn

3D & VIDEO TOUR

ABOUT THIS HOME
Home with a Pool for sale in Windsor County, VT:
Perched on a gentle knoll in the village, this inviting Cape-style home offers comfort, convenience, and room to grow. Ideally located just minutes from downtown Ludlow, enjoy easy access to the Okemo shuttle, local shops, dining, and the town’s vibrant community. The home has been meticulously maintained and thoughtfully updated with a remodeled kitchen and refreshed baths. Featuring three bedrooms and two bathrooms, it offers a warm, functional layout with built-in bedroom dressers, generous closet space, and abundant natural light throughout. An oversized two+-car garage provides excellent potential for expansion, (permits pending for finishing above) while the spacious deck and le

$520,000

3 beds2 baths2,350 sq ft

9 Deeplawn Ct, Ludlow, VT 05149

Remodeled kitchen • Refreshed baths • 0.44 acre lot

Property at 2170 Wildlife Rd, White River Junction, VT 05001, 4 beds, 2 baths

$650,000

4 beds2 baths2,496 sq ft

2170 Wildlife Rd, White River Junction, VT 05001

Property at 505 Cedarwood Rd, Stockbridge, VT 05772, 4 beds, 2.5 baths

$545,000

4 beds2.5 baths2,407 sq ft

505 Cedarwood Rd, Stockbridge, VT 05772

Property at 34 Midsomer Meadows Ln, Barnard, VT 05031, 3 beds, 3 baths

$950,000

3 beds3 baths2,794 sq ft

34 Midsomer Meadows Ln, Barnard, VT 05031

Property at 249 Sawyer Rd, Woodstock, VT 05091, 3 beds, 4.5 baths

$3,300,000

3 beds4.5 baths3,682 sq ft

249 Sawyer Rd, Woodstock, VT 05091

Property at 368 Crimson Hawk Rd, Plymouth, VT 05056, 3 beds, 2 baths

$560,000

3 beds2 baths1,552 sq ft

368 Crimson Hawk Rd, Plymouth, VT 05056

Property at 79 Clarina Nichols Ln, Hartford, VT 05059, 4 beds, 3 baths

$499,000

4 beds3 baths2,258 sq ft

79 Clarina Nichols Ln, Hartford, VT 05059

Property at 95 Union St, Springfield, VT 05156, 3 beds, 2 baths

$199,000

3 beds2 baths1,792 sq ft

95 Union St, Springfield, VT 05156

Property at 42 Cedar Dr, Ludlow, VT 05149, 4 beds, 3.5 baths

$1,400,000

4 beds3.5 baths4,487 sq ft

42 Cedar Dr, Ludlow, VT 05149

Property at 4205 VT Route 131, Perkinsville, VT 05151, 3 beds, 1.5 baths

$749,000

3 beds1.5 baths1,938 sq ft

4205 VT Route 131, Perkinsville, VT 05151

Property at 1269 Howard Hill Rd, Chester, VT 05143, 3 beds, 3 baths

$899,000

3 beds3 baths2,172 sq ft

1269 Howard Hill Rd, Chester, VT 05143

Property at 111 Lakeland Dr Unit D, Quechee, VT 05059, 2 beds, 2 baths

$495,000

2 beds2 baths1,346 sq ft

111 Lakeland Dr Unit D, Quechee, VT 05059

Property at 233 Trailside Ext Unit 45A, Ludlow, VT 05149, 4 beds, 2.5 baths

$855,000

4 beds2.5 baths1,842 sq ft

233 Trailside Ext Unit 45A, Ludlow, VT 05149

Property at 354 Grout Rd, Perkinsville, VT 05151, 3 beds, 3 baths

$599,000

3 beds3 baths2,898 sq ft

354 Grout Rd, Perkinsville, VT 05151

Property at 339 Ranney Rd, Stockbridge, VT 05772, 2 beds, 2.5 baths

$449,000

2 beds2.5 baths2,200 sq ft

339 Ranney Rd, Stockbridge, VT 05772

Property at 32 Plumley Ave, Ludlow, VT 05149, 3 beds, 3 baths

$585,000

3 beds3 baths3,062 sq ft

32 Plumley Ave, Ludlow, VT 05149

Property at 1726 Skitchewaug Trl, Springfield, VT 05156, 4 beds, 4.5 baths

$3,490,000

4 beds4.5 baths2,894 sq ft

1726 Skitchewaug Trl, Springfield, VT 05156

Property at 3773 woodstock Rd, White River Junction, VT 05001, 3 beds, 1 bath

$899,000

3 beds1 bath1,296 sq ft

3773 woodstock Rd, White River Junction, VT 05001

Property at 1051 Banister Rd, West Windsor, VT 05089, 3 beds, 3 baths

$695,000

3 beds3 baths3,490 sq ft

1051 Banister Rd, West Windsor, VT 05089

Property at 223 Taylor Dr, Windsor, VT 05089, 4 beds, 2.5 baths

$615,000

4 beds2.5 baths2,468 sq ft

223 Taylor Dr, Windsor, VT 05089

Property at 145 Main St #212, Ludlow, VT 05149, 2 beds, 1.5 baths

$220,000

2 beds1.5 baths1,019 sq ft

145 Main St #212, Ludlow, VT 05149

Property at 358 Cowdrey Path, South Woodstock, VT 05071, 3 beds, 2.5 baths

$895,000

3 beds2.5 baths2,048 sq ft

358 Cowdrey Path, South Woodstock, VT 05071

Property at 101 Okemo Trailside Ext Unit 41C, Ludlow, VT 05149, 3 beds, 2.5 baths

$729,000

3 beds2.5 baths1,842 sq ft

101 Okemo Trailside Ext Unit 41C, Ludlow, VT 05149

Property at 79 Merrill St, Springfield, VT 05156, 4 beds, 2.5 baths

$199,000

4 beds2.5 baths2,048 sq ft

79 Merrill St, Springfield, VT 05156

Property at 4946 South Rd, South Woodstock, VT 05071, 5 beds, 3.5 baths

$1,425,000

5 beds3.5 baths3,440 sq ft

4946 South Rd, South Woodstock, VT 05071

Property at 14 Gill Ter, Ludlow, VT 05149, 4 beds, 2 baths

$799,000

4 beds2 baths2,516 sq ft

14 Gill Ter, Ludlow, VT 05149

Property at 1497 Bowman Rd, South Royalton, VT 05031, 5 beds, 7 baths

$2,895,000

5 beds7 baths8,249 sq ft

1497 Bowman Rd, South Royalton, VT 05031

Property at 45 Kettlebrook Rd Unit J6, Ludlow, VT 05149, 3 beds, 2 baths

$749,000

3 beds2 baths1,531 sq ft

45 Kettlebrook Rd Unit J6, Ludlow, VT 05149

Property at 405 Soaring Hawk Rd, Plymouth, VT 05056, 3 beds, 2 baths

$550,000

3 beds2 baths1,728 sq ft

405 Soaring Hawk Rd, Plymouth, VT 05056

Property at 1362 Barnard Rd, Woodstock, VT 05091, 4 beds, 2 baths

$2,395,000

4 beds2 baths3,000 sq ft

1362 Barnard Rd, Woodstock, VT 05091

Property at 598 E Woodstock Rd, Woodstock, VT 05091, 4 beds, 3 baths

$795,000

4 beds3 baths3,190 sq ft

598 E Woodstock Rd, Woodstock, VT 05091

Property at 724 S Windsor St, South Royalton, VT 05068, 3 beds, 2 baths

$349,000

3 beds2 baths1,453 sq ft

724 S Windsor St, South Royalton, VT 05068

Property at 1846 Dartt Hill Rd, Bethel, VT 05032, 3 beds, 2 baths

$369,000

3 beds2 baths1,911 sq ft

1846 Dartt Hill Rd, Bethel, VT 05032

Property at 531 Main St, Chester, VT 05143, 3 beds, 1 bath

$425,000

3 beds1 bath1,608 sq ft

531 Main St, Chester, VT 05143

Property at 789 Ski Tow Rd #3, Brownsville, VT 05037, 1 bed, 1 bath

$147,500

1 bed1 bath602 sq ft

789 Ski Tow Rd #3, Brownsville, VT 05037

Property at 89 route 12, Hartland, VT 05048, 3 beds, 1 bath

$165,000

3 beds1 bath1,554 sq ft

89 route 12, Hartland, VT 05048

Property at 32 Melview Rdg, Norwich, VT 05055, 3 beds, 3 baths

$799,000

3 beds3 baths2,686 sq ft

32 Melview Rdg, Norwich, VT 05055

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Homes with Pools for Sale in Windsor County

There are currently 413 homes with pools for sale in Windsor County at a median listing price of $595K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Windsor County stay on the market for 114 days. This map is refreshed with the newest listings in Windsor County every 15 minutes.

In the past month, 87 homes have been sold in Windsor County. In addition to houses in Windsor County, there were also 94 condos, 4 townhouses, and 27 multi-family units for sale in Windsor County last month. Find your dream home in Windsor County using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Windsor County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Windsor County. If you're looking to sell your home in the Windsor County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Windsor County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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Copyright 2026 PrimeMLS All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this website comes in part from the VOW Program of PrimeMLS. Data last updated Sun Jan 04 2026 on the search page

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